James lay in bed stroking his erect young cock as he recounted his experience with Olivia. He had often imagined losing his virginity, but never imagined being seduced and pleasured with such a hot and sexy older woman. Compared with some rushed encounter with someone equally inexperienced, he had to pinch himself at the thought of Olivia's nubile body, skillful techniques, her willingness to suck his cock and make him cum, before getting him hard again and taking his cock in her lovely tight wet pussy.
He also found himself imagining Mrs Tyler the neighbour, and how turned on he was seeing her in her tight dresses and skirts and heels as she left for work and returned.
The following morning, the weather was cooler and it was cloudy and grey as he rode his bike up to Brian and Jan's house which was around a mile from the village. Olivia had said to be there for 9am and he made his way around to the kitchen where she was waiting wearing a skimpy silk nighty with spaghetti straps and lace edging.
"Good morning James"
James replied and she sat on the sofa in the large kitchen/diner/lounge area and patted the seat, inviting him to join her. Her tanned legs caught his eye, as did her gorgeous breasts, with semi erect nipples visible through her nightie.
James sat down and she started kissing him, as she had done the day before.
In between the erotic kisses and her sensual hand movements, she started probing into his sexual likes... "So what is it about Mrs Tyler that turns you on....tell me about her and what you imagine doing to her"
James felt a little embarrassed but also very aroused, as Olivia kissed his neck and whispered in his ear, with her hand brushing over his cock. She told his not to be shy and asked again...
"Well she's in her early 30's, slim with shoulder length brown hair, always looks smart going to work"
"What does she do and what kind of outfits does she wear James?"
James by now had a very hard cock and Olivia was squeezing it though his shorts... "She wears dresses and skirts, high heels, I have seen her in her bikini in the garden.."
"So you like ladies in heels and dresses James?" Does that look turn you on?"
Olivia asked again and she moved his hand to her swollen breast and erect nipple.
"I worked in a marketing agency...I spent my working week in dresses and heels...sometimes short skirts with black tights, sometimes longer dresses with holdups...always sexy lingerie...nice perfume... I liked to charm our male clients - looking good is good for business!" Do you think you'd fancy me if I was dressed like Mrs Tyler...?
James was now in a very aroused state and he replied "Yes" as Olivia released his cock, and he felt her warm lips around it. As she started to suck, she looked up, stopped momentarily and said "Good..."
The sensation of her licking and sucking his hard young cock was as amazing as the previous days, and he knew that he would soon end up cumming in her mouth again.
Olivia stopped after taking him deep in her mouth, and moved up to kiss him... "It's forecasting rain this afternoon....you'd better get on with that fence - come in for lunch at 12.30, I'm going into town but I'll be back before then...we will continue."
James was bemused at the sudden stop, his cock soon lost its rigidity as he put it away, Olivia gave him another playful kiss, before slipping her middle finger between her engorged and wet pussy lips, and cheekily licked it as her young lover prepared to head off to do his jobs.
Olivia had a plan, and once James was on his way, she headed into the master bedroom and her mothers wardrobe. Jan was in fantastic shape as she approached 50, and her and Olivia were both size 10 in dresses and size 5 in shoes. Having being Brian's PA, she had a great selection of very nice shift dresses, pencil skirts and tops (he funded her shopping trips long before they were officially a couple).
Olivia picked out a fitted grey dress, with buttons down the front, just above the knee, and also took out a paid of black heels. Her own suitcase contained a limited selection of her lingerie since she'd only packed a few basic items, with a view of spending most of her time in her bikini or topless! Having put the dress and heels in her own room, Olivia then pulled on some jeans and a T shirt and drove into Stratford and headed straight into M&S and their lingerie department. Within a few minutes she had selected a suitably sexy lacy black bra and knickers set, and picked up a pair of sheer black holdup stockings...smiling to herself at the thought of young James lusting after his neighbour. Olivia paid for her items and picked up a few items in the food hall, before heading home.
Olivia lay in the lovely spacious bath, her calves draped over the sides as she carefully and thoroughly shaved her pussy. Once it felt totally smooth, she did indulge in a little "me time" teasing her swollen clitoris and labia, but stopping short of climaxing...saving that moment until James' finger, tongue, or cock took her over the edge. She got out and dried off, moisturised and dried her hair, before lying naked on the bed browsing on her iPhone. Soon after midday, she got dressed, adjusting the bra straps to show her breasts off and pulling on the sheer holdups, smiling wryly at the thought of James...
12.30 arrived and James appeared at the door. Olivia appeared and his eyes were on stalks. She closed the door behind him and pressed him against the wall, kissing him on the lips, only stopping to say "Is this what Mrs Tyler looks like when she goes to work...? Is this what you imagine when you're wanking off in bed?...How do I look?"
James stammered a reply - this was beyond his wildest dream and fantasy. "You look amazing Olivia".
She walked across the kitchen and bent over, her shapely buttocks facing James. "Is this how she looks when you see her bend over at the car when she's going to work..?"
James replied, again completely mesmerised "Yes...you look so sexy".
Olivia faced him, running her hands over her breasts and down to her thighs. "Why don't you have a quick shower and meet me in my bedroom young man...I think you might like what's under this dress...you bad boy!"
James didn't need asking twice... his confidence had quadrupled in the short few days since Olivia set about educating him!
He stood in the spacious shower, soaping his armpits, and paying particular attention to his semi erect cock. Showers at home usually meant having a sneaky wank, spurting his cum towards the plughole as he imagined Mrs Tyler, or one of the other ladies who featured in his lustful young mind. This time he was showering ready to join the incredible Olivia in her sexy dress, heels and lingerie. He dried off and wrapped a towel around his waist before heading for her bedroom.
As he walked into the bedroom, Olivia told him to sit on the bed, before standing before him, and undoing a couple of top buttons on the dress to reveal the lacy black bra that barely covered her full firm breasts. Her hand slipped inside her bra and she teased her nipple, maintaining eye contact with James. Before moving closer, kissing him and undoing his towel and running her hand over his rapidly stiffening young cock. She then took his hand and placed it inside her dress and bra, licking her lips as he caressed and squeezed her erect nipple. Olivia's nipples were incredibly sensitive and became very prominent when aroused. In fact there had been several occasions when she had managed to climax totally from nipple play. As James sat naked, playing with her breast and nipples inside her lacy black bra, she could feel her pussy get wet...very wet in fact. He was gently stroking his cock which looked bigger and harder that the previous day.
Olivia moved back a little, giving James full view of her as she seductively bent over the end of the bed, lifting the rear of her dress as her naked young lover sat watching from the chair. The tension in the air was broken when she heard James say "Oh My God" as she revealed her lace topped stockings and the tanned bare thighs above them.
"You like?" She asked as she writhed before him.
"You are amazing...so sexy, I love it" James replied, his cock now rock hard at the sight before him. He clearly had a couple of fantasies or maybe fetishes, one being older women, the other being the classic sexy secretary look. This may have been fuelled by the frequent after school visits to the solicitors offices where his mother worked as he waited for a lift home from her. He was always very polite and well behaved, and would generally sit in reception and wait, enjoying the sight of the receptionists, secretaries and female solicitors who walked past him as they delivered and collected files. Heels, skirts, tights or maybe stockings, wafts of perfume, immaculate hair nails and makeup.
The sight of Olivia as she touched and exposed herself before him was like a pure fantasy come true. Part of him could not believe this was happening, part of him could not wait to touch her, taste her and basically fuck her!
Olivia then stood facing him, ran her hands up her nylon covered thighs and started touching herself through her transparent black knickers. She had learnt long ago that most men loved seeing a woman touch herself, and by the look of James face and his cock, he was clearly enjoying the show.
"Do you want to run your hands over my stockings James?"